


Sickchester Vol. 3

by Pineprin137



Series: Sickchester: The Complete Collection [3]
Category: Supernatural
Genre: Annoyed Sam Winchester, Burping, Caretaker Lisa, Caretaker Sam Winchester, Coughing, Gassy dean, He's not dying, Headaches & Migraines, Hurt/Comfort, If you've never had a migraine thank your lucky stars..., Influenza, Influenza sounds so serious..., Injured Dean Winchester, Sick Dean Winchester, Sickfic, Sneezing, Somewhat graphic!, Stomach Ache, Vomiting, Why isn't there a tag for "flu" yet????, Worried Sam Winchester, just sniffly, stomach flu, they suck.
Language: English
Status: Completed
Published: 2020-04-28
Updated: 2020-04-28
Packaged: 2021-03-01 17:00:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 3,877
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23900464
Author URL: https://archiveofourown.org/users/Pineprin137/pseuds/Pineprin137
Summary: Some of Dean's caretakers are better than others...
Series: Sickchester: The Complete Collection [3]
Series URL: https://archiveofourown.org/series/1683565
Comments: 9
Kudos: 46





	1. Stranded

**Author's Note:**

> All Dean in this one! I'll try to include some sick Sam soon, though!

“Dammit, Dean! Of course, you would get injured on an abandoned island! Not in a city, with access to medical care or even at one of the cabins… No, you had to wait until we’re stranded on a fucking tropical island to almost get your arm torn off by some unknown creature that no one’s ever heard of!” 

Sam paced the length of the small cave the brothers had luckily found before it started raining. Dean watched him for a few minutes but had to close his eyes when the constant movement made him dizzy. 

“I get it Sam... Things could be better, but--” 

Sam halted, spun to glare at him. “I  _ told  _ you this was a bad idea! I told you that something like this was going to happen, but  _ no _ , you just had to insist we come out here  _ during hurricane season! With no information on what we’re hunting! _ ” 

Dean winced, adjusting his position against the rock wall so he could cradle his left arm more securely against his body while Sam continued to rant. 

The  _ whatever-the-fuck _ had attacked him with what seemed like four-inch claws, but it all happened so fast, Dean wasn’t really sure. One second he had been walking beside Sam, doing recon on the beach where a few locals had been found mutilated, and the next he was being dragged into the jungle. 

Its massive claws had dug into his left shoulder, leaving deep lacerations that went almost through to the bone. His face and neck got scratched up by foliage, his clothes were caked with mud from the constant rain, and now, Sammy was yelling at him…  _ awesome _ . 

Once Sam had let out some of his pent-up frustration with their situation in the form of Dean's verbal lashing, his worry began to take hold. They were on an island off the coast of Maui with fewer than a hundred people, no way to contact the mainland since Dean’s phone got damaged and Sam’s died about an hour ago. The charter that brought them out there wasn’t due back for another three days and whatever they were hunting was still out there. It was getting dark outside the cave, and while Sam knew how to survive in the wilderness thanks to Bobby, there was a huge difference between South Dakota and Hawaii… 

Trying to hide how panicked he was beginning to feel, Sam sat down beside his brother. He peeked under the cloth covering Dean’s wound, kept his eyes down so Dean wouldn’t be able to see his growing concern.

“What are we going to do, Dean? We don’t have any way to contact anyone and your arm needs serious medical treatment,” Sam said, exasperated. 

If Bobby were here, he would slap Sam upside the head for the state of his Dean’s injured arm. Because even though they had used the last of their water to clean it, the wound was still littered with debris. At that point, infection was inevitable--it was  _ when  _ not  _ if _ . 

“I’ve had worse,” Dean said, trying to placate the guilt in his little brother’s voice. He wiped across his forehead with his uninjured arm and it came away glistening with sweat. Given their circumstances, either the humidity was rising or fever was starting to kick in. 

_ Damn _ . Dean was really starting to wish he’d listened to Sam back in Nevada. 

_ “There’s not enough information to go off, Dean! We don’t even know what did it and you want to charge in guns blazing? In the middle of HURRICANE SEASON!?”  _

Sam’s reasoning had been solid, but Dean ignored it anyway. He was itching to gut something and both Lucifer and the God squad had been quiet the last few weeks. So, they’d packed up, parked Baby in the long-term lot, and braved the four-hour flight to Maui. From there, they’d taken a small charter out to Molokai, AKA Leper Island.

Sam prodded his arm and Dean flinched. “ _ Son of a-- _ Watch it, would ‘ya?” he growled, trying to wiggle out of his brother’s grasp.

“Okay, yes, you’ve had worse,” Sam said, “But you also had access to medical care then, Dean. We’re on our own out here. Hell, I can’t even sew it up because that  _ thing _ took our bag!” 

Dean nodded grudgingly. “Yeah… that was  _ weird _ .” 

It was highly unusual for a monster to leave  _ wounded  _ prey in favor of stealing a bag full of random stuff. The hell would Klepto want with a bunch of medical supplies and clothes? There wasn’t even any ammo in the duffle-- the only weapons they brought were the machetes sitting on the cave floor beside them. So,  _ what  _ was it looking for…? 

He sucked in a sharp breath when Sam removed the makeshift bandage. His shoulder throbbed as soon as the air touched the exposed muscle and tendon. 

“How’s it look?” he asked, gritting his teeth so hard his jaw began to ache. 

Sam only glanced at him for about a second before he reached into his jacket pocket to pull out his pocket knife. It was the Swiss Army one that Jess got for him back at Stanford. It’d been almost five years since her death, but thanks to Dad and the importance he placed on weapon maintenance and upkeep, it was still in good condition. 

After opening each compartment to see what he had to work with, Sam chose the pliers. He used them to remove some of the detritus sticking to Dean’s torn bicep. With no x-ray available, Sam focused on taking out the bigger pieces so he could get a clearer picture of the extent of the damage. 

Dean tried to stay still while Sam dug around in his arm, but the pain was excruciating. Each little pluck or scrape felt like a layer of his skin being peeled off. After only a few minutes, Dean’s tolerance reached its limit. He begged Sam to stop. 

_ “Sammy… I can’t..." _ he gasped, _ "No more.” _

Dean’s entire body was shaking, his teeth chattering noisily in the silence of the cave. Sam hesitated then carefully cleaned off the tweezers as best he could with the cleanest part of his shirt and re-wrapped the bandage. 

“I think I got most of the big stuff, but Dean… ” 

“I know.” Dean turned to Sam, used his right hand to cup his brother’s face. “We’ll figure it out, okay? We always do.” 


	2. John

_ “Go lay down. That’s an order.” _

Sam looked up from his vocabulary worksheet when he heard his dad’s voice. He and Dean left around four to scope out the cemetery on the other side of town. The town had reported three mutilated corpses on the grounds in the last two weeks and when John saw the article in the paper, he had a hunch it was a ghoul. 

But they’d only been gone about twenty minutes so what were they doing back? 

“Dad?” Sam called out, walking into the hallway of the rundown house they were squatting in. 

John glanced up when Sam entered the kitchen. “You’re supposed to be working on your homework,” he said gruffly.

Sam shrugged. “I was, but I heard you guys come in. Did you find it?”

“No, we didn’t,” John said with a heavy sigh. He crossed his arms over his chest and nodded at the doorway that led to the living room. “Your brother’s sick. I came back to drop him off and get some supplies, then I’m heading back out.” 

When Sam walked over to the doorway to peer into the other room, he didn’t see Dean. Sam figured he’d probably be laying on the couch. The older teen had had a persistent headache for the last few days and then, last night, he also started coughing. But when John told him to get in the car earlier that morning to assist with scoping out the cemetery, Dean obeyed. 

“You’re going back out there--” Sam asked, turning back to John. “--alone?” 

Without answering, John brushed past him. He strode over to the couch, smacked the back of it. Sam rolled his eyes. That couldn’t have helped Dean’s headache. 

John crossed his arms, staring at the lump on the couch. “I told you to lay down.” 

Dean opened his eyes, confused. He remembered coming home and lying down. Had he not? He turned his head, saw the back of the couch. No, he was definitely still on the ratty couch. 

“Huh?” He asked his dad. The older man must’ve recognized his disorientation as the beginnings of fever because, instead of berating Dean for not listening, he sighed and gestured to Sam. 

“Sam, help your brother into your room. I’m going to grab a few things then head out. I overheard someone at the diner saying the sheriff’s posting someone at the graveyard tonight and I want to get there before he does.” 

“Yes, sir,” Sam mumbled, walking to the front to the couch. 

Dean was sitting there, his hair mussed, looking half-dead. His face was pale except for his cheeks which had a nice rosy hue to them. Dean coughed, squinting against the dim light. Definitely the flu, Sam thought. 

When Dean coughed a second time, Sam saw flecks of  _ something _ spray from his mouth. He grimaced. “Dude, gross,” he complained, “Cover your mouth.” 

“...  _ Sammy? _ ” Dean asked, giving him a funny look.

“Duh. Who else would it be?” Sam replied. 

Dean frowned, trying to figure out what his brother was doing at the cemetery. He twisted one way then the other, but he didn’t see John anywhere. That was probably a good thing-- Dad would blow a gasket if he found out Sammy tagged along… 

Sam waved a hand in front of his brother’s face. “Dean? Hello?” He didn’t get a response. With a heavy sigh, he leaned down so he could slide one arm around Dean’s waist. Then-- with great effort-- he hauled Dean off the couch. 

The sick teen swayed dangerously, almost taking both of them to the floor. 

_ “What’re you doing here?”  _ Dean mumbled, his head lolling against Sam’s. _ “Dad told you to stay back…”  _

“I did-- you and Dad came back,” Sam explained as he led Dean down the hallway. He nudged the bedroom door open with his foot. It had a tendency to close on its own-- just an old house, not a ghost-- they’d checked first thing. 

“You’re sick, dude. Dad told you to lay down and you passed out on the couch.” 

_ “Oh,”  _ Dean said quietly. Sam risked a quick glance at him and found Dean’s eyes half-closed. 

With a loud grunt, he deposited his brother on the rickety bed. It smelled like old lady, but it was comfier than the floor and there was a pretty nice crocheted blanket too. After they’d dusted it off the first day, the boys had realized it was probably handmade. 

As Dean slumped to the right, Sam removed his heavy jacket and boots, then instructed him to lay down. Dean did, immediately curling into a ball. Sam covered him with the blanket-- which Dean promptly hacked into-- then grabbed his notebook and worksheet from the end of the bed before crawling up beside his brother. After placing the lone pillow beneath Dean’s head, Sam picked up his pencil and got back to work.  __


	3. Research

When a loud whine split the air of the library Sam glanced up from the lore book in front of him. He saw Dean wince before placing a hand on his belly. 

“Was that your stomach?” Sam asked, incredulous. 

“Yeah, sorry,” Dean replied. 

Sam squinted at his brother but didn't see anything out of place. “You okay?” he said. 

Dean shrugged. “Yeah. 'Was something I ate, I think.” 

They returned to their research. Sam had just pulled up an article in one of the town’s newspapers about a sighting of a large black dog when he heard the noise again. 

He sighed, peering around the side of his laptop, “Why don’t you take a Tums or something?” 

“I did,” Dean said with a grimace. “Don’t worry about it.” 

Sam held up his hands in surrender. “Okay, geez.” 

After a few minutes, Dean spoke again. 

“Did you find anything on Fido?” he asked, smoothing a hand over his churning stomach. Sam nodded and turned the laptop toward him. While Dean scrolled through the webpage, he paraphrased the police report.

“Two girls were walking through the woods on the edge of town. Apparently a large black dog came out of the shadows and attacked the first girl.” 

Dean burped softly then looked at him. “What about the second girl? Fluffy get her too?” 

Sam shook his head. “No. She got away while it was eating her friend. ” 

Dean snorted. “Lucky girl." He nodded at the sheaf of printed papers located on the table in front of and around Sam. "Any other attacks?" 

"Not yet," Sam supplied. 

Dean hummed then leaned back in his chair. "Local cops roped off the area yet?” 

Sam sighed. “You know, you could just read the article instead of asking me…” 

Dean smirked. “Where’s the fun in that?” 

Sam rolled his eyes and explained that although the sheriff’s office hadn’t officially blockaded the woods where the girls were attacked, they had released a statement encouraging people to stay away from the area. Nodding to show Sam he was still listening, Dean stood up. 

He stretched his arms up over his head then winced and pressed his fist to his chest and belched loudly. When he started walking toward the hallway, Sam narrowed his eyes. 

“Dean, where are you going?” He gestured at the books and papers strewn over the table. “We may have figured out the black dog, but we still need to look into the disappearance at the high school.” 

His brother paused at the top of the steps to give him a (not-so) innocent look. “Bathroom break,” he said, rubbing a hand over his bloated belly. 

Sam called after him as he left the room, “I better not find you in your room watching Casa Erotica!” 

Smirking, Dean responded with a loud belch before continuing down the hall to his room. __

After changing into a pair of loose sweats, he headed to the bathroom in search of relief. He sighed when he saw the bright pink bottle on the counter where he’d left it earlier. Beelining straight for it, Dean took a healthy swig of the chalky liquid hoping it would settle his stomach. He hadn’t been lying when he told Sam it was probably something he ate. He’d been experiencing some serious indigestion since last night and had broken out the Pepto when he started feeling a little sick around five.

A loud gurgle echoed throughout the empty room and he grimaced, breathing heavily as the pressure in his gut continued to intensify. Reluctantly admitting defeat, Dean walked over to one of the stalls.

  
  


Sam glanced up from his reading when the words on the screen began to blur. Checking the clock, he realized they’d worked through lunch. Sighing, he leaned back in his chair and covered his eyes with his hand only to lower it back down when he caught sight of Dean’s chair. It was empty. Thoroughly annoyed that he’d been, once again, tricked into doing all of the research, Sam scowled before marking his place and closing his laptop. 

He stalked down the hallway towards his brother’s room but paused when he heard loud grunting come from the direction of the bathroom. Somewhat concerned-- but mostly still angry-- Sam decided to investigate. 

When he entered the large bathroom, he saw his brother sitting in one of the stalls. The door was wide open and Dean looked miserable. Sam took a careful step forward, but his shoe squeaked against the tiled floor anyway, announcing his presence. 

Dean looked up at the noise and huffed loudly. “Oh, _come on!_ Can’t a guy take a shit in peace?!” 


	4. Migraine

**Notes for the Chapter:**

> Inspired by the one I had last week. It was sooo much fun... not.

Dean woke with a headache. Not a terrible one, but rather an annoying throb behind one eye that refused to go away. However, by the time he and Sam finished morning training with Dad, it had multiplied. Now, both eyes were pulsing and his vision was a little blurry. Oh, and the sound of Sam gathering his breakfast supplies made Dean want to _sock him in the face..._ But other than that, he was fine... With a sigh, he sat down at the table. 

_ Clang!  _

Sam’s spoon dropped into the empty bowl. Dean winced before burying his head in his arms.  _ Jesus, why are the lights so fucking bright all of a sudden… _

“Dude, what’s with you today?” Sam asked when Dean pushed away his unused bowl in favor of resting his head. Dean grunted.

When Sam shook cereal into his bowl, it sounded like an avalanche. Then, _g_ _ lug glug glug... Thud!  _ The bottom of the milk jug hit the surface of the table and Dean felt the vibration through his entire body. There was a loud _scrrrreeeech_ as Sam pulled his chair out and finally sat down. 

Dean clenched his jaw. _How_ _ can one kid make so much fucking noise?!? _

“I’m fine. Just a headache,” he mumbled, finally answering Sam's earlier question. 

“Uh-huh…” his brother said, disbelieving. 

Dean lifted his head to glare at him- weakly and without the usual accompanying eye-roll because he’s pretty sure he would puke if he tried. 

“Don’t you have homework to finish or something?” he grumbled.

“Already finished it,” Sam said matter-of-factly, taking another bite of cereal. 

_Crunch. Crunch. Crunch._ Every bite  caused a sharp pain behind Dean’s left eye. He dug his heel against it, wishing he could remove the damn thing entirely... He flinched when Sam's spoon bounced off the side of the bowl with a loud - _T_ _i_ _ng!-._

“Did you take anything?” Sam asked, pointing to the bathroom with the offending spoon. Dean wanted to snatch it from his brother's hand and chuck it out the window. Instead, he shook his head.

“I think we still have some pain meds in the medkit," Sam continued, "Unless Dad used ‘em all last night.” Dean nodded distractedly.

However, after a few minutes, he shuffled over to the familiar green canvas bag. He dug around until he found a white bottle with a red cap. The - _ pop!-  _ of the lid reverberated in Dean’s ears. He gritted his teeth. After quickly shaking out two capsules, he swallowed them with a handful of water from the tap. 

Turning to the toilet, Dean closed the lid. He sat down, massaging between his eyebrows, desperate to ease the ache. It seemed every time he moved or spoke or blinked, the pain in his head got worse. At the table, it had simply been an annoying thump behind his eyes, but now, in the harsh fluorescent lighting of the bathroom, vice-like pressure crawled across his forehead to nestle deep in his temples. 

The soft  _ shh shh shh _ of shoes on the old carpet alerted Dean to Sam's arrival. He stopped in the doorway. Dean prayed he wouldn't speak but knew it was inevitable.

“We have to head out in like, five minutes--” Sam said. He entered the bathroom and walked over to Dean. _Tap tap. Tap_. _Tap tap_ went his hesitant steps on the old laminate. 

“Are you okay, Dean? You look kind of pale…” Dean gritted his teeth as the sound of Sam's voice scraped along the inside of his skull. 

“I’m fine,” he said, slowly rising from the toilet and walking over to the sink. He turned on the faucet but had to grip the edge of the counter when it sounded like a waterfall to his sensitive ears. 

He took a slow breath. “I told you-” Another breath. Nice and slow... He could do this. “It’s just a headache. I’ll be fi-” 

Dean spun, shoving Sam out of the way as he crashed onto his knees, fumbled the lid up, and vomited. 

" _Right-”_ Sam said with a sigh. He grabbed a washcloth from the edge of the sink and wet it under the tap then placed it on the back of Dean’s neck. 

“- just a headache… ” 


	5. Lisa

Dean definitely wasn’t used to this-- laying on a fuzzy pink bathmat instead of a dingy motel floor while waiting for the inevitable. On cue, his stomach gurgled noisily. He winced. 

“Just breathe, honey,” Lisa whispered as she blotted his forehead with the damp washcloth held in her hand. 

Bitter liquid shot up Dean’s throat. He hastily re-positioned himself so his head hung over the toilet bowl. Lisa gently rubbed his back, her hand brushing over his grey tee-shirt soothingly. 

As a mom, she was used to staying up with Ben when he got sick. And while it had taken about an hour of speaking through a locked bathroom door, Lisa had eventually convinced Dean to let her take care of him as well. 

The retired hunter groaned before another mouthful of brown liquid splashed noisily into the bowl. God, he almost wished it was a curse rather than the stomach flu. At least with a curse, there was usually an easy answer-- kill the witch/ box up the cursed object/ complete the spell-- but  _ this _ ? All Dean could do was wait it out. 

The next heave that tore up his throat was dry, hopefully signaling the end. Dean squeezed his eyes shut mostly to block the sight of his former stomach contents in the toilet bowl, but also because it  _ fucking hurt! _

“Easy, honey… It’s almost over,” Lisa soothed, holding him steady as his body attempted to wring out every last bit it could. 

Two gut-wrenching coughs and a pitiful amount of bile later, Dean flopped back onto the floor with an arm tossed over his eyes and the other cradling his stomach. Lisa rubbed his shoulder, her brow creasing with sympathy. She knew how awful the flu could be and this strain seemed particularly nasty. 

After flushing the toilet, she wiped Dean’s mouth off with the damp cloth then picked up the cup sitting on the floor by her knee. She propped his head up, held the cup to his lips. With a weary sigh, Dean allowed her to help him take a few small sips. 

They stayed there for a few minutes, Lisa carding her fingers through Dean’s sweaty hair. When she spoke, her voice was barely louder than a whisper. 

“Ready to get off the floor?” she asked.

Dean responded by licking his chapped lips and mumbling, “I don’t know if that’s a good idea.” 

She couldn’t help a small chuckle. “I put the trash can on your side of the bed and a bowl on the nightstand, just in case. So, I think you’ll be okay.” 

Dean opened his eyes, looked up at her. He was somewhat surprised she was willing to risk her pristine bedding… 

“Really?” he asked dubiously. 

Lisa nodded. “I can always throw them in the wash if you don’t...  _ make it _ …” 

Dean blushed, remembering the last time he hadn’t quite gotten to the toilet in time after a night out with some of the guys from work. 

Lisa carefully stood up then held her hands out. “Come on, big guy, let’s get you up so we can put you to bed.” 


End file.
